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Compare 21 Condo Rentals in Healdsburg with updated reviews, rates, and availability.

Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Pool
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
9.2 out of 10, Wonderful, (7)
"Think of this place as a home away from home. It has everything you need to cook meals and fridge, dishwasher, washer and dryer, oven with some baking sheets. I would recommend that if you are going to be doing the majority of cooking there to bring your own oils, spices, aluminum foil and plastic wrap. The unit was immaculate! All the units have a grill and patio furniture. The bathrooms were super clean and spacious! My unit had an extra bed in the living room, Murphy bed."
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
3.0 star property
8.4 out of 10, Very Good, (8)
"Enjoyed location and proximity to Healdsburg."
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (39)
"The location is very convenient to Kendall-Jackson and many other vineyards. The condo was clean and comfortable for a one night stay. We weren’t there long enough to speak to other details aside from comfortable beds. We weren’t aware that this was a vacation club condo complex and the very hard sell we would be met with. We had flown cross country all day then a drive up from San Francisco. All we wanted was to settle in and grab some dinner. The town of Windsor was fabulous and we enjoyed...
The price is AED 1,377
AED 2,780 total
includes taxes & fees
30 Nov - 1 Dec
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Wine Country Beautiful Worldmark 2Bedroom Resort
Pool
Wine Country Beautiful Worldmark 2Bedroom Resort
9.4 out of 10, Exceptional, (65)
"A comfortable, up-to-date alternative to hotels in the area, with plenty of resort-style and family-friendly amenities."
Wine Country Beautiful Worldmark 2Bedroom Resort
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
9.6 out of 10, Exceptional, (27)
"Very nice and convenient place. Only hiccup was checking in. It was to be available at 4 pm. Did not get our room till 7 pm"
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Great Wine Country and Golfing Resort Getaway!!
Exterior
Great Wine Country and Golfing Resort Getaway!!
8.0 out of 10, Very Good, (2)
"The property was very clean and easy to get around. They offered many amenities and have a very nice outdoor area to hang out. "
Great Wine Country and Golfing Resort Getaway!!
WorldMark Windsor - 1 Bedroom
Windsor_pool_3_S
WorldMark Windsor - 1 Bedroom
2.0 star property
9.0 out of 10, Wonderful, (2)
"The condo was very clean and had everything needed for a relaxing stay. The pool was also wonderful with no overcrowding! "
WorldMark Windsor - 1 Bedroom
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Pool
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
WorldMark Windsor - 2 Bedroom Twin
Windsor_pool_S
WorldMark Windsor - 2 Bedroom Twin
2.0 star property
8.0 out of 10, Very Good, (1)
"Very clean, convenient location, good facilities. Comfortable beds. Well equipped kitchen. Pool was a good size, hot tubs and pool open till 10 pm which was nice after a long day. I had only 2 issues, one that there was no free wifi. I was told before I booked that it would be free for my unit but was given no info. on how to access it for free, Apparently I needed some info. that no one was able to give me so I ended up having to pay for it. And the second of course is the pressure...
WorldMark Windsor - 2 Bedroom Twin
WorldMark Windsor - 2 Bedroom
Windsor_pool_3_S
WorldMark Windsor - 2 Bedroom
2.0 star property
9.6 out of 10, Exceptional, (4)
"We needed to stay close to family and were able to spend time with them. Also getting to the airport lead so convenient. "
WorldMark Windsor - 2 Bedroom
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Pool
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
3.5 star property
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Living area
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
WorldMark Windsor - 3 Bedroom Deluxe
Windsor_pool_S
WorldMark Windsor - 3 Bedroom Deluxe
2.0 star property
WorldMark Windsor - 3 Bedroom Deluxe
WorldMark Windsor - 2 Bedroom Accessible
Windsor_pool_3_S
WorldMark Windsor - 2 Bedroom Accessible
2.0 star property
WorldMark Windsor - 2 Bedroom Accessible
WorldMark Windsor - 3 Bedroom
Windsor_pool_S
WorldMark Windsor - 3 Bedroom
2.0 star property
WorldMark Windsor - 3 Bedroom
WorldMark Windsor - 3 Bedroom Penthouse Accessible
Windsor_pool_S
WorldMark Windsor - 3 Bedroom Penthouse Accessible
2.0 star property
WorldMark Windsor - 3 Bedroom Penthouse Accessible
WorldMark Windsor - 1 Bedroom Accessible
Windsor_pool_3_S
WorldMark Windsor - 1 Bedroom Accessible
2.0 star property
WorldMark Windsor - 1 Bedroom Accessible
WorldMark Windsor - 3 Bedroom Accessible
Windsor_pool_S
WorldMark Windsor - 3 Bedroom Accessible
2.0 star property
WorldMark Windsor - 3 Bedroom Accessible
WorldMark Windsor - 3 Bedroom Penthouse
Windsor_pool_S
WorldMark Windsor - 3 Bedroom Penthouse
2.0 star property
WorldMark Windsor - 3 Bedroom Penthouse
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Living area
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Healdsburg

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Bliss House Panorama View 1
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
10.0 out of 10, Exceptional, (227)
"Comfortable house, just outside town, with fantastic views of vineyards and the whole valley. We used the well equipped kitchen and enjoyed eating on the porch while looking at the colorful fall vines. Great place to stay while wine tasting."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
First Crush Cottage
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (153)
"The cottage and the grounds are absolutely gorgeous! We loved the way the cottage was decorated, so cozy! Everything was well appointed. There are multiple places on the grounds to sit and enjoy a glass of wine and the scenery. It is the perfect size for two couples. The location is close to downtown Healdsburg, Dry Creek wineries and a five-minute walk to the Dry Creek General Store! Napa is only a little over an hour away. The owners and property manager responded quickly when we had...
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Enjoy lawns, gardens, and a walk in through our vineyards
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, (230)
"Just like the pictures. Grounds were gorgeous & the stay was very relaxing. My family had a wonderful time. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do condos in Healdsburg cost?
You’ll pay from AED 1,377 to AED 1,377 per night for condos in Healdsburg. Whatever your budget, an ideal stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Healdsburg?
Choose from 21 condos in Healdsburg. No matter if you’re traveling with the little ones or getting away with your pals, Expedia can help you find the perfect space for your entire crew.
Why book your condo in Healdsburg with Expedia?
With Expedia, you’ll have no trouble finding your dream condo in Healdsburg. On the lookout for someplace luxurious? Find your way to the filters to search for properties that are 5-star rated. If you have a budget, choose how much you want to spend and then browse our incredible deals. We’ll help you find the perfect pad whatever your escape looks like.
How can I find cheap condos in Healdsburg?
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